House holiday rentals in Pioneer Valley

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Pioneer Valley

House rentals with a pool

Guest favourite
Home in Colrain
4.9 out of 5 average rating, 129 reviews

The 1770 House

CatherineRating, 5 stars1 month ago
Historic house on a beautiful property. Kitchen had all the equipment you could need along with top of the line stove and oven. Make cooking for a large group easy and enjoyable!
Top guest favourite
Home in Westhampton
5 out of 5 average rating, 27 reviews

Happy Valley getaway

ChrisRating, 5 stars6 days ago
We had a wonderful stay in Westhampton. The place itself had plenty to do and was well stocked with amenities. The owners were also very proactive in letting us know about an issue with the previous renters that resulted in a deeper cleaning than expected. Nevertheless, we recommend Jen’s house and would definitely stay there again.
Superhost
Home in Wilmington
4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

Catherine (Lou)Rating, 5 stars4 months ago
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.
Guest favourite
Home in Keene
4.93 out of 5 average rating, 211 reviews

The Brick House on Washington Street

PaulRating, 5 stars1 week ago
Great stay and was exactly what we needed for our entire family for a weekend wedding!
Top guest favourite
Home in Wilmington
4.96 out of 5 average rating, 28 reviews

Family/Dog Friendly Mountain Home w/ Amenities

LouisRating, 5 stars3 days ago
Jake’s home is outstanding. The beds are very comfortable. The internet is good, The home has lots of space , a great kitchen with all amenities that we needed. Gas stove etc. The outlay was very comfortable and made for the perfect vacation. I’ve stayed at many homes in the area, Jake’s place is by far the best. We also went to the Clubhouse and used the pool and hot tub which was an added surprise.
Top guest favourite
Home in Chesterfield
4.98 out of 5 average rating, 59 reviews

High Field Farm

TracyRating, 5 stars4 days ago
⸻ A perfect countryside escape! This was our second stay at High Field Farm, and it was just as amazing as the first. The farmhouse is beautiful, with spectacular woodland views from every window that make it feel like a peaceful retreat. It’s incredibly relaxing and well-stocked with all the essentials you could need. Everything was spotless and exactly as described. Jenny is a wonderful host—warm, responsive, and thoughtful. We’re already looking forward to our next visit. Highly recommend to anyone looking for a tranquil getaway in nature!
Top guest favourite
Home in Lanesborough
5 out of 5 average rating, 22 reviews

Mountain Blossom Retreat by Evergreen Home

AlysonRating, 5 stars3 weeks ago
We selected this amazing property as the location for our mini-wedding and we could not have been happier. The house is brilliant in every way. The floor plan, the furnishings, the decor, and the grounds are all thoughtful and stunningly beautiful. The property manager was always responsive and kind. This is truly a top property and you will not be disappointed. We cannot wait to visit again.
Guest favourite
Home in Northampton
5 out of 5 average rating, 14 reviews

Sun-drenched 6BR Victorian steps from downtown

KevinRating, 5 stars3 weeks ago
I wish I had known about this property sooner for my visits to Amherst College. It was better than advertised. Sunny, clean, comfortable and so close to walk to town. My whole family enjoyed it very much.

Weekly house rentals

Superhost
Home in Windsor Locks
5 out of 5 average rating, 3 reviews

Warm Woodland Retreat

DaniRating, 5 stars5 days ago
Zach is really proactive and kind. He left me alone , which is what I needed for this short trip, but made me feel like if I needed anything (recommendations, assistance, communications) he would be responsive and quick. The place is a cool New England house with a lot of charm. The neighbors are respectful and quiet. Youre minutes away from a lot of great Connecticut icons and Uber is accessible and cheap. I hope to stay here agin when I return in Sept. The upstairs room is challenging if there are mobility concerns - I would try to book the lower levels. All was wonderful and Zach was kind.
Top guest favourite
Home in Belchertown
4.99 out of 5 average rating, 72 reviews

Moonstone Lake House – romantic, serene, fun!

RochelleRating, 5 stars6 days ago
Had a wonderful stay at Mighty’s house on the lake. It was such a peaceful and beautiful area. The house was clean and tidy with a spacious bathroom and comfortable bed. It was reassuring to have our hosts right next door but there was a good amount of privacy. We enjoyed the fire pit in the evenings, taking the canoe out on the beautiful lake and having some space and time to wind down. I highly recommend this home for anyone looking to step away from life for a little while.
Guest favourite
Home in Springfield
4.94 out of 5 average rating, 93 reviews

Clean/Spacious 1 bedroom house. Kitchen, LR, DR.

FeliciaRating, 5 stars2 weeks ago
We really enjoyed our stay here. House was comfy and clean on a beautiful quiet street. Plenty of off road parking. There were little extras throughout the house that was very convenient, although we didn't need it, there were plenty of toiletries and snacks! Maria was an excellent host very attentive to making our stay comfortable as possible.
Guest favourite
Home in Ashfield
4.98 out of 5 average rating, 57 reviews

An 18th century farmhouse

NateRating, 5 stars1 week ago
What a beautiful, idyllic getaway Susan offers for her guests. A kind welcoming soul who provides a stay that brings you back in history – we had the most lovely time!
Guest favourite
Home in Ashfield
4.98 out of 5 average rating, 87 reviews

Magical, Rural Getaway in the Berkshires

SarahRating, 5 stars3 weeks ago
This place was great, I was a little concerned it may be too rustic based on the pictures, but the place was fabulous. No problems with wifi, access, sleeping arrangements. The open space for the kitchen/tv room were so great for our large family. Everything is well appointed, there are clear instructions everywhere on how to use anything in the house. It was really nice for our short weekend stay for graduation. I felt the kitchen was better stocked than most places I've stayed. They had everything we needed. I wish we could have used the fireplace on this rainy cold weekend, but heard maybe it's an Airbnb thing not an owner thing. If you want to head to this area, this was a great place to stay.
Guest favourite
Home in Amherst
5 out of 5 average rating, 9 reviews

Amherst Treehouse

JoannaRating, 5 stars3 weeks ago
We were three couples coming together for a college reunion in the area. The house fit our needs perfectly with plenty of space to relax and cook. The fireplace was a godsend during a May nor'easter. Victoria left detailed instructions and welcomed us with thoughtful touches like popcorn and local restaurant recommendations. We just can't recommend it enough if you're looking in the area. Our only regret was that we were unable to enjoy the outdoor fire pit given the weather.
Guest favourite
Home in Northampton
4.92 out of 5 average rating, 38 reviews

The Walnut Apartment

JuliaRating, 5 stars1 week ago
Very cute apartment and more than what we needed for a one night stay on a wedding weekend! The downstairs has a charming sitting room and spacious kitchen with fridge, stove, and laundry. The stairs were a bit steep so be cautious! Upstairs a comfy soft bed with window AC and a large bathroom with clawfoot tub/shower. Jennifer was very nice about our last minute request to check in early to change for a 4 PM wedding. We would stay here again if we come back to the area! Thanks so much!
Guest favourite
Home in Guilford
4.92 out of 5 average rating, 50 reviews

Vermont Mirror House

GeorgeRating, 5 stars1 week ago
I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.

Private house rentals

Top guest favourite
Home in Ashfield
5 out of 5 average rating, 16 reviews

J&J’s Retreat

SeanRating, 5 stars6 months ago
What a retreat! This was a lovely stay in a beautiful home which was well decorated and every little detail was thoughtful. Our family enjoyed our stay - thank you!
Top guest favourite
Home in Shelburne Falls
5 out of 5 average rating, 97 reviews

Charming Brookside Artisan Home

NellieRating, 5 stars2 weeks ago
This place was awesome. Would have enjoyed the outdoors and fire pit more if it didn’t rain. I would definitely recommend
Guest favourite
Home in Northampton
4.77 out of 5 average rating, 22 reviews

Home in Northampton

HelenRating, 5 stars5 days ago
Terry was amazing. We had an issue and couldn't check in on time and Terry worked with us. If we could come back and stay we definitely would!
Top guest favourite
Home in Village of Pelham
4.96 out of 5 average rating, 49 reviews

Amherst/Pelham getaway with a view!

AlyssaRating, 5 stars5 days ago
Lauren was a great host - very accommodating and easy to communicate with. She gave great recommendations and also had extra amenities for our baby which was so helpful. Recommend!
Top guest favourite
Home in New Hartford
4.96 out of 5 average rating, 69 reviews

Private Woodland Sanctuary—3 mins to a lake beach!

EmilyRating, 5 stars2 weeks ago
this place is magical. my sisters and I have stayed here twice now, for her wedding and now for mine. both times the home has been clean and the overall experience has been wonderful.
Guest favourite
Home in Lanesborough
4.96 out of 5 average rating, 51 reviews

Historic Stone Church in The Berkshires

ZacharyRating, 5 stars3 weeks ago
Our stay at Hinterland Hall was a wonderful, unique experience. The property has been carefully restored and tastefully staged. The surrounding area includes some great hikes, like Mount Graylock to the north and Monument Mountain to the south.
Top guest favourite
Home in Leyden
5 out of 5 average rating, 15 reviews

Mountaintop Views, close to private schools, golf

JasonRating, 5 stars1 week ago
Beautiful property! Fantastic deck and views, and spacious and modern inside. Great place for a weekend with friends!
Superhost
Home in Agawam
4.82 out of 5 average rating, 28 reviews

Home near Six Flags/ hot tub

MariaRating, 5 stars1 month ago
This home is just what the pictures show. It was a great first experience with Airbnb. Checking in and out was simple. The only thing we noticed is that one of the bathroom’s trash was not thrown out. Other than that, no other issues. The home is very nice and clean. Just an FYI for future renters, the house is in a Main Street but we didn’t mind the minimal traffic noise, mostly at night, since we live in a big city and are used to it. We would stay here again.

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